The document discusses various topics related to pharmacognosy and phytochemistry, including different classes of plant-derived compounds and specific examples. It begins with a general introduction and overview of alkaloids, describing their properties, classification, extraction methods, and important historical discoveries. Specific alkaloids discussed include those found in belladonna, such as hyoscyamine, atropine, and apoatropine. The chemical constituents and tests used to identify alkaloids are also summarized.

1. SSBE’S
Nanded Pharmacy College, Nanded
Pharmacognosy & Phytochemistry –II
BP504 T
Dr M H Ghante

2. Unit-II
Contents
• General introduction,
• composition,
• chemistry & chemical
classes,
• general methods of
extraction &
• analysis,
• biosources,
• therapeutic uses and
• commercial applications
1. Alkaloids: Vinca, Rauwolfia, Belladonna,
Opium,
2. Phenylpropanoids and Flavonoids: Lignans, Tea, Ruta
3. Steroids, Cardiac Glycosides & Triterpenoids: Liquorice,
Dioscorea, Digitalis
4. Volatile oils: Mentha, Clove, Cinnamon, Fennel,
Coriander,
5. Tannins: Catechu, Pterocarpus
6. Resins: Benzoin, Guggul, Ginger, Asafoetida, Myrrh,
Colophony
7. Glycosides: Senna, Aloes, Bitter Almond
8. Iridoids, Other terpenoids & Naphthaquinones:
Gentian, Artemisia, taxus, carotenoids
• General introduction,
• composition,
• chemistry & chemical
classes,
• general methods of
extraction &
• analysis,
• biosources,
• therapeutic uses and
• commercial applications
1. Alkaloids: Vinca, Rauwolfia, Belladonna,
Opium,
2. Phenylpropanoids and Flavonoids: Lignans, Tea, Ruta
3. Steroids, Cardiac Glycosides & Triterpenoids: Liquorice,
Dioscorea, Digitalis
4. Volatile oils: Mentha, Clove, Cinnamon, Fennel,
Coriander,
5. Tannins: Catechu, Pterocarpus
6. Resins: Benzoin, Guggul, Ginger, Asafoetida, Myrrh,
Colophony
7. Glycosides: Senna, Aloes, Bitter Almond
8. Iridoids, Other terpenoids & Naphthaquinones:
Gentian, Artemisia, taxus, carotenoids 2
Edited & Compiled by Dr M H Ghante

3. Alkaloids:
Vinca, Rauwolfia, Belladonna, Opium,
• General introduction,
• composition,
• chemistry & chemical classes,
• general methods of extraction &
• analysis,
• biosources,
• therapeutic uses and
• commercial applications
• General introduction,
• composition,
• chemistry & chemical classes,
• general methods of extraction &
• analysis,
• biosources,
• therapeutic uses and
• commercial applications
3
Edited & Compiled by Dr M H Ghante

4. Overall biosynthetic pathways in plants
4
Edited & Compiled by Dr M H Ghante

5. Alkaloids
Vinca, Rauwolfia, Belladonna, Opium,
• General Introduction
• ‘Alkaloid’ (alkali-like) ≈≈naturally occurring complex amines.
• Their amine character produce an alkaline solution in water and hence the origin
of their name—alkaloids.
• Alkaloids often contain one or more rings of carbon atoms, usually with a nitrogen
atom in the ring (usually in a heterocyclic ring) .
• The position of the nitrogen atom in the carbon ring varies with different alkaloids
and with different plant families.
• In fact, it is the precise position of the nitrogen atom that affects the properties of
these alkaloids ≈≈ SAR.
• General Introduction
• ‘Alkaloid’ (alkali-like) ≈≈naturally occurring complex amines.
• Their amine character produce an alkaline solution in water and hence the origin
of their name—alkaloids.
• Alkaloids often contain one or more rings of carbon atoms, usually with a nitrogen
atom in the ring (usually in a heterocyclic ring) .
• The position of the nitrogen atom in the carbon ring varies with different alkaloids
and with different plant families.
• In fact, it is the precise position of the nitrogen atom that affects the properties of
these alkaloids ≈≈ SAR.
5
Edited & Compiled by Dr M H Ghante

6. Alkaloids
Vinca, Rauwolfia, Belladonna, Opium,
General Introduction
• And that’s why they usually have a marked and varied physiological action on
man or other animals.
• These compounds are renowned for their potent pharmacological activities.
• Even though many alkaloids are
– poisonous (e.g. strychnine or coniine),
• Whilst tiny amounts of some can immobilize an elephant or a rhinoceros,
others have important clinical use, such as
– analgesics, (morphine and codeine)
– Antimalarial (Quiinine),
– antispasmodics,
– anti-cancer (paclitaxel)
– for pupil dilation (atropine),
– treatment of hypertension, mental disorders.
General Introduction
• And that’s why they usually have a marked and varied physiological action on
man or other animals.
• These compounds are renowned for their potent pharmacological activities.
• Even though many alkaloids are
– poisonous (e.g. strychnine or coniine),
• Whilst tiny amounts of some can immobilize an elephant or a rhinoceros,
others have important clinical use, such as
– analgesics, (morphine and codeine)
– Antimalarial (Quiinine),
– antispasmodics,
– anti-cancer (paclitaxel)
– for pupil dilation (atropine),
– treatment of hypertension, mental disorders.
6
Edited & Compiled by Dr M H Ghante

7. History
History
• Narcotine in 1803 and
• opium and isolated morphine g (1806, 1816).
• Strychnine (1817),
• emetine (1817),
• Brucine (1819),
• piperine (1819),
• caffeine (1819),
• quinine (1820),
• Colchicine (1820) and
• coniine (1826).
• Coniine was the first alkaloid to have its structure established (Schiff, 1870)
and to be synthesized (Ladenburg, 1889), but for others, such as colchicine
• 1800-1940  150 alkaloids
• 1940-2000 10000 alkaloids from over 300 plant families (advent of
sophisticated/ modern instruments)
History
• Narcotine in 1803 and
• opium and isolated morphine g (1806, 1816).
• Strychnine (1817),
• emetine (1817),
• Brucine (1819),
• piperine (1819),
• caffeine (1819),
• quinine (1820),
• Colchicine (1820) and
• coniine (1826).
• Coniine was the first alkaloid to have its structure established (Schiff, 1870)
and to be synthesized (Ladenburg, 1889), but for others, such as colchicine
• 1800-1940  150 alkaloids
• 1940-2000 10000 alkaloids from over 300 plant families (advent of
sophisticated/ modern instruments) 7
Edited & Compiled by Dr M H Ghante

8. Alkaloids:
Vinca, Rauwolfia, Belladonna, Opium,
CLASSIFICATION
• Alkaloids are divided according to their shapes and origins.
• There are three main types of alkaloids:
– (1) true alkaloids, -quinine, dopamine and morphine.
– (2) protoalkaloids, and
– (3) pseudoalkaloids- coniine, capsaicin, ephedrine, solanidine, caffeine and
– theobromine
• True alkaloids and protoalkaloids are derived from amino acids,
• whereas pseudoalkaloids are not derived from these compounds.
There are two broad divisions:
I. Non-heterocyclic or atypical alkaloids, sometimes called ‘protoalkaloids’ or
biological amines.
II. Heterocyclic or typical alkaloids, divided into 14 groups according to their ring
structure.
CLASSIFICATION
• Alkaloids are divided according to their shapes and origins.
• There are three main types of alkaloids:
– (1) true alkaloids, -quinine, dopamine and morphine.
– (2) protoalkaloids, and
– (3) pseudoalkaloids- coniine, capsaicin, ephedrine, solanidine, caffeine and
– theobromine
• True alkaloids and protoalkaloids are derived from amino acids,
• whereas pseudoalkaloids are not derived from these compounds.
There are two broad divisions:
I. Non-heterocyclic or atypical alkaloids, sometimes called ‘protoalkaloids’ or
biological amines.
II. Heterocyclic or typical alkaloids, divided into 14 groups according to their ring
structure. 8
Edited & Compiled by Dr M H Ghante

9. Alkaloids- Classsification
9
Edited & Compiled by Dr M H Ghante

10. Alkaloids- Classsification
10
Edited & Compiled by Dr M H Ghante

11. Alkaloids- Classsification
11
Edited & Compiled by Dr M H Ghante

12. Alkaloids- Classsification
12
Edited & Compiled by Dr M H Ghante

13. Alkaloids- Classsification
13
Edited & Compiled by Dr M H Ghante

14. Alkaloids- Classsification
14
Edited & Compiled by Dr M H Ghante

15. Alkaloids- Classsification
15
Edited & Compiled by Dr M H Ghante

16. 16
Edited & Compiled by Dr M H Ghante

17. 17
Edited & Compiled by Dr M H Ghante

18. Alkaloids- Extraction methods
Process A.
• The powdered material is moistened with
water and mixed
• with lime which combines with acids,
tannins and other phenolic substances
• and sets free the alkaloids (if they exist in
the plant as salts).
• Extraction is then carried out with organic
solvents such as ether or petroleum spirit.
• The concentrated organic liquid is then
shaken with aqueous acid and allowed to
separate.
• Alkaloid salts are now in the aqueous
liquid, while many impurities remain
behind in the organic liquid.
Process B
• The powdered material is
extracted with water or aqueous
alcohol containing dilute acid.
• Pigments and other unwanted
materials are removed by shaking
with chloroform or other organic
solvents.
• The free alkaloids are then
precipitated by the addition of
excess sodium bicarbonate or
ammonia and
• separated by filtration or by
extraction with organic solvents.
• The powdered material is moistened with
water and mixed
• with lime which combines with acids,
tannins and other phenolic substances
• and sets free the alkaloids (if they exist in
the plant as salts).
• Extraction is then carried out with organic
solvents such as ether or petroleum spirit.
• The concentrated organic liquid is then
shaken with aqueous acid and allowed to
separate.
• Alkaloid salts are now in the aqueous
liquid, while many impurities remain
behind in the organic liquid.
• The powdered material is
extracted with water or aqueous
alcohol containing dilute acid.
• Pigments and other unwanted
materials are removed by shaking
with chloroform or other organic
solvents.
• The free alkaloids are then
precipitated by the addition of
excess sodium bicarbonate or
ammonia and
• separated by filtration or by
extraction with organic solvents.
18
Edited & Compiled by Dr M H Ghante

19. Alkaloids- Chemical Tests
The chemical tests are performed from neutral or slightly acidic
solution of drug.
1. Dragendorff’s Test- Drug solution + Dragendroff ’s reagent (Potassium Bismuth Iodide),
formation of Orangish red colour.
2. Mayer’s Test-Drug solution + few drops of Mayer’s reagent (potassium mercuric iodide),
formation of creamy-white precipitant.
3. Hager’s Test-Drug solution + few drops of Hagers reagent (Saturated aq. Solution of Picric acid),
formation of crystalline yellow precipitate.
4. Wagner’s Test- Drug solution + few drops of Wagner’s reagent (dilute Iodine solution),
formulation of reddish-brown precipitate.
5. Tannic Acid Test- Drug solution + few drops of tannic acid solution, formation of buff coloured
precipitate.
6. Ammonia Reineckate Test- Drug solution + slightly acidified (HCl) saturated solution of ammonia
reineckate, formation of pink flocculent precipitate.
The chemical tests are performed from neutral or slightly acidic
solution of drug.
1. Dragendorff’s Test- Drug solution + Dragendroff ’s reagent (Potassium Bismuth Iodide),
formation of Orangish red colour.
2. Mayer’s Test-Drug solution + few drops of Mayer’s reagent (potassium mercuric iodide),
formation of creamy-white precipitant.
3. Hager’s Test-Drug solution + few drops of Hagers reagent (Saturated aq. Solution of Picric acid),
formation of crystalline yellow precipitate.
4. Wagner’s Test- Drug solution + few drops of Wagner’s reagent (dilute Iodine solution),
formulation of reddish-brown precipitate.
5. Tannic Acid Test- Drug solution + few drops of tannic acid solution, formation of buff coloured
precipitate.
6. Ammonia Reineckate Test- Drug solution + slightly acidified (HCl) saturated solution of ammonia
reineckate, formation of pink flocculent precipitate.
19
Edited & Compiled by Dr M H Ghante

20. Alkaloids: Belladonna
• BELLADONNA
• Synonyms-Belladonna herb; Belladonna leaf; Deadly night
shade leaves; Banewort; Death’s herb, Dwale; Poison black
cherry; Folia belladonnae.
• Biological Source-Belladonna consists of dried leaves and
flowering tops of Atropa belladonna Linn. (European
Belladonna),
• belonging to family Solanaceae.
• It contains about 0.35% of total alkaloids calculated as
hyoscyamine.
• Geographical Source-A. belladonna is cultivated in United
States, Canada, UK, Germany and India.
• BELLADONNA
• Synonyms-Belladonna herb; Belladonna leaf; Deadly night
shade leaves; Banewort; Death’s herb, Dwale; Poison black
cherry; Folia belladonnae.
• Biological Source-Belladonna consists of dried leaves and
flowering tops of Atropa belladonna Linn. (European
Belladonna),
• belonging to family Solanaceae.
• It contains about 0.35% of total alkaloids calculated as
hyoscyamine.
• Geographical Source-A. belladonna is cultivated in United
States, Canada, UK, Germany and India.
20
Edited & Compiled by Dr M H Ghante

21. Alkaloids
Belladona Leaves -Chemical Constituents
• Belladonna contains 0.3–1.0% total alkaloids,
• the prominent base is l-hyoscyamine and
– atropine, used for dilating pupils and as gastrointestinal sedative)
– apoatropine, as choline,
– belladonnine,
– cuscohygrine,
– Chrysatropic acid,
– volatile bases, such as atroscine, leucatropic acid;
– phytosterol,
– N-methylpyrroline, homatropine, hyoscyamine
– N-oxide,
– rutin, kaempferol-3-rhamnogalactoside and 7-glucoside, quercetin-7-glucoside,
– scopoletin,
– calcium oxalate, 14% acid soluble ash and 4% acid-insoluble ash.
• Belladonna contains 0.3–1.0% total alkaloids,
• the prominent base is l-hyoscyamine and
– atropine, used for dilating pupils and as gastrointestinal sedative)
– apoatropine, as choline,
– belladonnine,
– cuscohygrine,
– Chrysatropic acid,
– volatile bases, such as atroscine, leucatropic acid;
– phytosterol,
– N-methylpyrroline, homatropine, hyoscyamine
– N-oxide,
– rutin, kaempferol-3-rhamnogalactoside and 7-glucoside, quercetin-7-glucoside,
– scopoletin,
– calcium oxalate, 14% acid soluble ash and 4% acid-insoluble ash.
21
Edited & Compiled by Dr M H Ghante

22. Alkaloids:
Belladona roots- Chemical Constituents
• Constituents. Atropa belladonna root contains about 0.4–0.8% of
alkaloids calculated as hyoscyamine.
• Showed 0.3–1.0% of alkaloids, of which
– 82.8–97.3% was hyoscyamine,
– 2.7–15.2% atropine, and
– 0.0–2.6% scopolamine.
• Capillary GLC–mass spectrometry data revealed the presence of
• hygrine,
• hygroline,
• cuscohygrine,
• tropinone,
• tropine,
• pseudotropine and
• nine tropanol esters
• Other constituents previously reported include
– belladonnine together with β-methylaesculetin, calcium oxalate & starch.
• Constituents. Atropa belladonna root contains about 0.4–0.8% of
alkaloids calculated as hyoscyamine.
• Showed 0.3–1.0% of alkaloids, of which
– 82.8–97.3% was hyoscyamine,
– 2.7–15.2% atropine, and
– 0.0–2.6% scopolamine.
• Capillary GLC–mass spectrometry data revealed the presence of
• hygrine,
• hygroline,
• cuscohygrine,
• tropinone,
• tropine,
• pseudotropine and
• nine tropanol esters
• Other constituents previously reported include
– belladonnine together with β-methylaesculetin, calcium oxalate & starch.22
Edited & Compiled by Dr M H Ghante

23. Alkaloids: Belladona: Uses
• The drug is used as adjunctive therapy in the treatment of peptic ulcer;
• functional digestive disorders, including spastic, mucous and ulcerative colitis;
diarrhoea, diverticulitis and pancreatitis.
• Due to anticholinergic property, it is used to control excess motor activity of the
gastrointestinal tract and spasm of the urinary tract.
• Belladonna is
– anticholinergic,
– narcotic,
– sedative,
– Diuretic
– mydriatic and
– used as anodyne and to check secretion.
• Other uses are similar to Hyoscyamus.
• It relieves spasm of gut or respiratory tract.
• Consumption of Belladonna checks excessive perspiration of patients suffering from
tuberculosis.
• Belladonna acts as a parasympathetic depressant.
• The drug is used as adjunctive therapy in the treatment of peptic ulcer;
• functional digestive disorders, including spastic, mucous and ulcerative colitis;
diarrhoea, diverticulitis and pancreatitis.
• Due to anticholinergic property, it is used to control excess motor activity of the
gastrointestinal tract and spasm of the urinary tract.
• Belladonna is
– anticholinergic,
– narcotic,
– sedative,
– Diuretic
– mydriatic and
– used as anodyne and to check secretion.
• Other uses are similar to Hyoscyamus.
• It relieves spasm of gut or respiratory tract.
• Consumption of Belladonna checks excessive perspiration of patients suffering from
tuberculosis.
• Belladonna acts as a parasympathetic depressant.
23
Edited & Compiled by Dr M H Ghante

24. • Addition of ammonia to the alcoholic solution of
scopoletin shows blue florescence. This test is useful
to detect Belladonna poisoning.
• Atropine is formed by racemization during the
extraction process.
• Marketed Products
• It is one of the ingredients of the preparation known as
• Belladona plaster (Surgi Pharma) for
– backache,
– stiffness of muscles and boil,
– swollen joints.
• Addition of ammonia to the alcoholic solution of
scopoletin shows blue florescence. This test is useful
to detect Belladonna poisoning.
• Atropine is formed by racemization during the
extraction process.
• Marketed Products
• It is one of the ingredients of the preparation known as
• Belladona plaster (Surgi Pharma) for
– backache,
– stiffness of muscles and boil,
– swollen joints.
24
Edited & Compiled by Dr M H Ghante

25. Alkaloids: Opium
Biological Source
• Opium is the air dried milky latex obtained by incision from the
unripe capsules of Papaver somniferum Linn, or its variety P. album
Decand., belonging to family Papaveraceae.
• Opium is required to contain not less than 10% of morphine and
not less than 2.0% of codeine.
• The thebaine content is limited to 3%.
Geographical Source
• It is mainly found in Turkey, Russia, Yugoslavia, Tasmania,
• India, Pakistan, Iran, Afghanistan, China, Burma, Thailand
• and Laos.
• In India, Opium is cultivated in M.P. (Neemuch) and U.P. for
alkaloidal extraction and seed production.
Biological Source
• Opium is the air dried milky latex obtained by incision from the
unripe capsules of Papaver somniferum Linn, or its variety P. album
Decand., belonging to family Papaveraceae.
• Opium is required to contain not less than 10% of morphine and
not less than 2.0% of codeine.
• The thebaine content is limited to 3%.
Geographical Source
• It is mainly found in Turkey, Russia, Yugoslavia, Tasmania,
• India, Pakistan, Iran, Afghanistan, China, Burma, Thailand
• and Laos.
• In India, Opium is cultivated in M.P. (Neemuch) and U.P. for
alkaloidal extraction and seed production.
25
Edited & Compiled by Dr M H Ghante

26. Alkaloids: Opium-History
• Hippocrates ‘the father of medicine’, (460–357 B.C.) prescribed drinking the
juice of the white poppy mixed with the seed of nettle and also
acknowledged its use as narcotic and styptic in internal diseases.
• It was Alexander the Great, who introduced opium to India and Persia.
• During the 17th century tobacco smoking was introduced in China, which
resulted in its extensive.
• In 1805 Friedrich W. Seiturner (German pharmacist) isolated and identified
the chief chemical constituent of opium.
• The compound isolated was named morphium (morphine) after Morpheus,
the god of dreams.
• Eventually many other constituents like codeine (1832) and papaverine
(1848) were also isolated and identified.
• Due to the uncontrolled use of opium in china (late 18th century) the imperial
court had to ban its use.
• 1898 a German company manufactured 3, 6-diacetylmorphine (Heroin) in
bulk quantity.
• Hippocrates ‘the father of medicine’, (460–357 B.C.) prescribed drinking the
juice of the white poppy mixed with the seed of nettle and also
acknowledged its use as narcotic and styptic in internal diseases.
• It was Alexander the Great, who introduced opium to India and Persia.
• During the 17th century tobacco smoking was introduced in China, which
resulted in its extensive.
• In 1805 Friedrich W. Seiturner (German pharmacist) isolated and identified
the chief chemical constituent of opium.
• The compound isolated was named morphium (morphine) after Morpheus,
the god of dreams.
• Eventually many other constituents like codeine (1832) and papaverine
(1848) were also isolated and identified.
• Due to the uncontrolled use of opium in china (late 18th century) the imperial
court had to ban its use.
• 1898 a German company manufactured 3, 6-diacetylmorphine (Heroin) in
bulk quantity.
26
Edited & Compiled by Dr M H Ghante

27. Alkaloids: Opium-History
• In December 1914, Harrison Narcotics Act which called for control of each
phase of the preparation and distribution of medicinal opium, morphine,
heroin, cocaine, and any new derivative with similar properties, was enforced
by the United States Congress.
• The Federal Controlled Substances Act of 1970 is the redefined act of the
Harrison Act.
• In 1999, opium was declared as the Bumper crop of Afghanistan by producing
75% of world’s heroin.
• In December 2002 the U.K. government under the health plan, will make
heroin available free on National Health Service to all those with a clinical
need for it.
• In December 1914, Harrison Narcotics Act which called for control of each
phase of the preparation and distribution of medicinal opium, morphine,
heroin, cocaine, and any new derivative with similar properties, was enforced
by the United States Congress.
• The Federal Controlled Substances Act of 1970 is the redefined act of the
Harrison Act.
• In 1999, opium was declared as the Bumper crop of Afghanistan by producing
75% of world’s heroin.
• In December 2002 the U.K. government under the health plan, will make
heroin available free on National Health Service to all those with a clinical
need for it. 27
Edited & Compiled by Dr M H Ghante

28. Alkaloids: Opium-Chemical Constituents
• Opium contains about 35 alkaloids among which morphine (10–16%) is the most important
base.
• The alkaloids are combined with meconic acid.
– The other alkaloids isolated from the drug are codeine (0.8–2.5%),
– narcotine, thebaine (0.5–2%).
– noscapine (4–8%),
– narceine and papaverine (0.5–2.5%).
– Morphine contains a phenanthrene nucleus.
• The different types of alkaloids isolated are:
• Morphine Type: Morphine, codeine, neopine, pseudo or oxymorphine, thebaine and
porphyroxine.
• Morphine consists of alkaloids which has phenanthrene nucleus whereas those of the
papaverine group has benzylisoquinoline structure.
• Protopine and hydrocotamine are of different structural types.
• The morphine molecule has both a phenolic and an alcoholic hydroxyl group and acetylated
form is diacetyl morphine or heroin.
• Codeine is ether of morphine (methyl-morphine).
• Other morphine ethers which are used medicinally are ethylmorphine and pholcodine.
• Opium contains about 35 alkaloids among which morphine (10–16%) is the most important
base.
• The alkaloids are combined with meconic acid.
– The other alkaloids isolated from the drug are codeine (0.8–2.5%),
– narcotine, thebaine (0.5–2%).
– noscapine (4–8%),
– narceine and papaverine (0.5–2.5%).
– Morphine contains a phenanthrene nucleus.
• The different types of alkaloids isolated are:
• Morphine Type: Morphine, codeine, neopine, pseudo or oxymorphine, thebaine and
porphyroxine.
• Morphine consists of alkaloids which has phenanthrene nucleus whereas those of the
papaverine group has benzylisoquinoline structure.
• Protopine and hydrocotamine are of different structural types.
• The morphine molecule has both a phenolic and an alcoholic hydroxyl group and acetylated
form is diacetyl morphine or heroin.
• Codeine is ether of morphine (methyl-morphine).
• Other morphine ethers which are used medicinally are ethylmorphine and pholcodine.
28
Edited & Compiled by Dr M H Ghante

29. • 2. Phthalide Isoquinoline Type:
• Hydrocotarnme, narcotoline, 1-narcotine, noscapine, oxynarcotine, narceine,
and 5’-O-demethyl-narcotine.
• 3. Benzyl Isoquinoline Type:
Papaverine, dl-laudanine, laudanidine, codamine and laudanosine.
• 4. Cryptopine Type:
Protopine, cryptopine.
• 5. Unknown Constituents:
Aporeine, diodeadine, meconidine, papaveramine and lanthopine.
The drug also contains sugars, sulphates, albuminous compounds, colouring
matter and moisture.
In addition to these anisaldehyde, vanillin, vanillic acid, β-hydroxystyrene, fumaric
acid, lactic acid, benzyl alcohol, 2-hydroxycinchonic acid, phthalic acid,
hemipinic acid, meconin and an odorous compound have also been reported.
Alkaloids: Opium-Chemical Constituents
• 2. Phthalide Isoquinoline Type:
• Hydrocotarnme, narcotoline, 1-narcotine, noscapine, oxynarcotine, narceine,
and 5’-O-demethyl-narcotine.
• 3. Benzyl Isoquinoline Type:
Papaverine, dl-laudanine, laudanidine, codamine and laudanosine.
• 4. Cryptopine Type:
Protopine, cryptopine.
• 5. Unknown Constituents:
Aporeine, diodeadine, meconidine, papaveramine and lanthopine.
The drug also contains sugars, sulphates, albuminous compounds, colouring
matter and moisture.
In addition to these anisaldehyde, vanillin, vanillic acid, β-hydroxystyrene, fumaric
acid, lactic acid, benzyl alcohol, 2-hydroxycinchonic acid, phthalic acid,
hemipinic acid, meconin and an odorous compound have also been reported.
29
Edited & Compiled by Dr M H Ghante

30. Alkaloids: Opium- Chemical Tests & Uses
• Chemical Tests
1. Aqueous extract of Opium with FeCl3 solution gives deep reddish purple colour
which persists on addition of HCl. It indicates the presence of meconic acid.
2. Morphine gives dark violet colour with conc. H2SO4 and formaldehyde.
• Uses
1. Opium and morphine have narcotic, analgesic and sedative action and used
to relieve pain, diarrhoea dysentery and cough.
2. Poppy capsules are astringent, somniferous, soporific, sedative and narcotic
and used as anodyne and emollient.
3. Codeine is mild sedative and is employed in cough mixtures.
4. Noscapine is not narcotic and has cough suppressant action acting as a
central anti-tussive drug.
5. Papaverine has smooth muscle relaxant action and is used to cure muscle
spasms. Opium, morphine and the diacetyl derivative heroin, cause drug
addiction.
• Chemical Tests
1. Aqueous extract of Opium with FeCl3 solution gives deep reddish purple colour
which persists on addition of HCl. It indicates the presence of meconic acid.
2. Morphine gives dark violet colour with conc. H2SO4 and formaldehyde.
• Uses
1. Opium and morphine have narcotic, analgesic and sedative action and used
to relieve pain, diarrhoea dysentery and cough.
2. Poppy capsules are astringent, somniferous, soporific, sedative and narcotic
and used as anodyne and emollient.
3. Codeine is mild sedative and is employed in cough mixtures.
4. Noscapine is not narcotic and has cough suppressant action acting as a
central anti-tussive drug.
5. Papaverine has smooth muscle relaxant action and is used to cure muscle
spasms. Opium, morphine and the diacetyl derivative heroin, cause drug
addiction.
30
Edited & Compiled by Dr M H Ghante

31. • Manufacture of opium alkaloids.
• The majority of legal opium is used for the isolation of its constituent
alkaloids, and in
• Britain some 90% of the morphine produced is converted into other bases
such as codeine, ethylmorphine and pholcodine.
• In recent years attempts have been made to reduce the illicit traffic in opium
either by banning the cultivation of the opium poppy or by cultivation under
strict licences.
• However, two methods by which the opium stage is eliminated are by
extraction of the whole poppy capsule and by the use of other species (e.g. P.
bracteatum) which do not contain morphine.
• Manufacture of opium alkaloids.
• The majority of legal opium is used for the isolation of its constituent
alkaloids, and in
• Britain some 90% of the morphine produced is converted into other bases
such as codeine, ethylmorphine and pholcodine.
• In recent years attempts have been made to reduce the illicit traffic in opium
either by banning the cultivation of the opium poppy or by cultivation under
strict licences.
• However, two methods by which the opium stage is eliminated are by
extraction of the whole poppy capsule and by the use of other species (e.g. P.
bracteatum) which do not contain morphine. 31
Edited & Compiled by Dr M H Ghante

32. Extraction of poppy capsules and straw
• The feasibility of extracting poppy straw has long been known and utilized in Europe
and recently there has been a world-wide trend towards the extraction of the dried
poppy capsules (e.g. in Hungary, former USSR, Tasmania).
• In a study of poppy capsule drying and storage under commercial conditions in
Tasmania it has been shown that kiln-drying of immature capsules (42 days old) at
various temperatures (40–100°C) resulted in a loss of morphine content of up to about
11% without effect on codeine and thebaine.
• However, this morphine loss was significantly less than with the field-dried material.
• To avoid deterioration of the dried product the moisture content should not exceed
16%.
• Processes have also been developed in France and in the UK for the harvesting and
processing of the green capsule, one technical difficulty being the separation of the
seed from the fruit at this stage of development.
• The feasibility of extracting poppy straw has long been known and utilized in Europe
and recently there has been a world-wide trend towards the extraction of the dried
poppy capsules (e.g. in Hungary, former USSR, Tasmania).
• In a study of poppy capsule drying and storage under commercial conditions in
Tasmania it has been shown that kiln-drying of immature capsules (42 days old) at
various temperatures (40–100°C) resulted in a loss of morphine content of up to about
11% without effect on codeine and thebaine.
• However, this morphine loss was significantly less than with the field-dried material.
• To avoid deterioration of the dried product the moisture content should not exceed
16%.
• Processes have also been developed in France and in the UK for the harvesting and
processing of the green capsule, one technical difficulty being the separation of the
seed from the fruit at this stage of development.
32
Edited & Compiled by Dr M H Ghante

33. Alkaloids:Rauwolfia
• Synonyms
Sarpagandha, Chandrika; Chootachand; Indian snake root.
• Biological Source
Rauwolfia consists of dried roots of Rauwolfia serpentina Benth., belonging to
family Apocynaceae.
• Geographical Source
• It is an erect, evergreen, small shrub native to the Orient and occurs from India
to Sumatra. It is also found in Burma, Thailand, Philippines, Vietnam, Indonesia,
Malaysia, Pakistan and Java.
• In India it occurs in the sub-Himalayan tracts from Sirhind eastwards to Assam,
especially in Dehradun, Siwalik range, Rohelkhand, Gorakhpur ascending to
1,300 m, east and west ghats of Tamil Nadu, in Bihar (Patna and Bhagalpur),
Konkan, Karnataka and Bengal.
• Synonyms
Sarpagandha, Chandrika; Chootachand; Indian snake root.
• Biological Source
Rauwolfia consists of dried roots of Rauwolfia serpentina Benth., belonging to
family Apocynaceae.
• Geographical Source
• It is an erect, evergreen, small shrub native to the Orient and occurs from India
to Sumatra. It is also found in Burma, Thailand, Philippines, Vietnam, Indonesia,
Malaysia, Pakistan and Java.
• In India it occurs in the sub-Himalayan tracts from Sirhind eastwards to Assam,
especially in Dehradun, Siwalik range, Rohelkhand, Gorakhpur ascending to
1,300 m, east and west ghats of Tamil Nadu, in Bihar (Patna and Bhagalpur),
Konkan, Karnataka and Bengal.
33
Edited & Compiled by Dr M H Ghante

34. Alkaloids: Rauwolfia
Chemical Constituents
• Rauwolfia contains about 0.7–2.4% total alkaloidal bases from which more than 80 alkaloids
have been isolated.
• The prominent alkaloids isolated from the drug are
– reserpine, ψ-reserpine, (ψ=psi)
– rescinnamine,
– rescidine,
– raubescine and
– deserpidine.
• The other alkaloidal components are
– ajmalinine, ajmaline, ajmalicine (8-yohimbine),
– serpentine, serpentinine,
– tetrahydroreserpine,
– raubasine,
– reserpinine,
– isoajamaline and yohambinine.
• The other substances present are phytosterols, fatty acids, unsaturated alcohols and sugars.
Chemical Constituents
• Rauwolfia contains about 0.7–2.4% total alkaloidal bases from which more than 80 alkaloids
have been isolated.
• The prominent alkaloids isolated from the drug are
– reserpine, ψ-reserpine, (ψ=psi)
– rescinnamine,
– rescidine,
– raubescine and
– deserpidine.
• The other alkaloidal components are
– ajmalinine, ajmaline, ajmalicine (8-yohimbine),
– serpentine, serpentinine,
– tetrahydroreserpine,
– raubasine,
– reserpinine,
– isoajamaline and yohambinine.
• The other substances present are phytosterols, fatty acids, unsaturated alcohols and sugars.
34
Edited & Compiled by Dr M H Ghante

35. Alkaloids: Rauwolfia-Uses
• Rauwolfia in used as hypnotic, sedative and antihypertensive.
• cures pain due to affection of the bowels.
• It is given in labours to increase uterine contractions and in certain
neuropsychiatric disorders.
• Ajmaline- for the treatment of cardiac arrhythmias.
• Reserpine is an antihypertensive and tranquilizer.
• Rescinnamine is the methyl reserpate ester of 3,4,5-trimethoxy cinnamic acid.
• The usual antihypertensive dose of rescinnamine is 500 μg, two times a day.
Higher doses may cause serious mental depression.
• Deserpidine is 11-des-methoxyreserpine. It is a wide-range tranquilizer and
antihypertensive and is free from the side effects.
Marketed Products
• It is one of the ingredients of the preparations known as Confido, Lukol,
Serpina (Himalaya Drug Company) and Sarpagandhan bati (Baidyanath).
• An estimated 3500 kg of ajmalicine is isolated annually from either
Rauwolfia or Catharanthus spp. b
• Rauwolfia in used as hypnotic, sedative and antihypertensive.
• cures pain due to affection of the bowels.
• It is given in labours to increase uterine contractions and in certain
neuropsychiatric disorders.
• Ajmaline- for the treatment of cardiac arrhythmias.
• Reserpine is an antihypertensive and tranquilizer.
• Rescinnamine is the methyl reserpate ester of 3,4,5-trimethoxy cinnamic acid.
• The usual antihypertensive dose of rescinnamine is 500 μg, two times a day.
Higher doses may cause serious mental depression.
• Deserpidine is 11-des-methoxyreserpine. It is a wide-range tranquilizer and
antihypertensive and is free from the side effects.
Marketed Products
• It is one of the ingredients of the preparations known as Confido, Lukol,
Serpina (Himalaya Drug Company) and Sarpagandhan bati (Baidyanath).
• An estimated 3500 kg of ajmalicine is isolated annually from either
Rauwolfia or Catharanthus spp. b 35
Edited & Compiled by Dr M H Ghante

36. Alkaloids:Vinca
• Synonyms
Vinca rosea, Catharanthus, Madagascar periwinkle. Barmasi.
• Biological Source
Vinca is the dried entire plant of Catharanthus roseus Linn.,
belonging to family Apocynaceae.
• Geographical Source
The plant is a native of Madagascar and is found in many
tropical and subtropical countries especially in India, Australia, South
Africa and North and South America.
The plant is cultivated as garden plant in Europe and India.
• Synonyms
Vinca rosea, Catharanthus, Madagascar periwinkle. Barmasi.
• Biological Source
Vinca is the dried entire plant of Catharanthus roseus Linn.,
belonging to family Apocynaceae.
• Geographical Source
The plant is a native of Madagascar and is found in many
tropical and subtropical countries especially in India, Australia, South
Africa and North and South America.
The plant is cultivated as garden plant in Europe and India.
36
Edited & Compiled by Dr M H Ghante

37. Alkaloids:Vinca
History.
• Although the plant has a certain reputation in folk medicine
for the treatment of diabetes, modern investigators have been
unable to confirm this property.
• Instead Canadian workers, during 1955–1960, discovered that extracts of
the leaves produced leukopenic actions in rats.
• These observations led researchers at Eli Lilly to undertake an intensive
phytochemical investigation of the plant with a view to the isolation of
constituents of value in cancer chemotherapy.
• Six alkaloids proved active in this respect and two are now available
• commercially
History.
• Although the plant has a certain reputation in folk medicine
for the treatment of diabetes, modern investigators have been
unable to confirm this property.
• Instead Canadian workers, during 1955–1960, discovered that extracts of
the leaves produced leukopenic actions in rats.
• These observations led researchers at Eli Lilly to undertake an intensive
phytochemical investigation of the plant with a view to the isolation of
constituents of value in cancer chemotherapy.
• Six alkaloids proved active in this respect and two are now available
• commercially
37
Edited & Compiled by Dr M H Ghante

38. Alkaloids:Vinca
Constituents.
• About 150 alkaloids have now been isolated from
C. roseus;
• some, for example, ajmalicine, lochnerine, serpentine and
• tetrahydroalstonine, occur in other genera of the family.
• Of particular interest is a group of about 20 bisindole alkaloids which contains those having
antineoplastic activity, including
– leurocristine (vincristine) and
– vincaleukoblastine (vinblastine).
– Vinblastine is produced by coupling of the indole alkaloids catharanthine and vindoline,
both of which occur free in the plant.
– Vincristine is structurally similar to vinblastine, but has a formyl group rather than a
methyl on the indole nitrogen in the vindoline-derived portion.
– vincristine is obtained in about 0.0002% yield from the crude drug
• In addition, there is a growing demand for vincristine rather than vinblastine, but the plant
produces a much higher proportion of vinblastine.
• Fortunately, it is now possible to convert vinblastine into vincristine either chemically, or via
a microbiological N-demethylation using Streptomyces albogriseolus.
Constituents.
• About 150 alkaloids have now been isolated from
C. roseus;
• some, for example, ajmalicine, lochnerine, serpentine and
• tetrahydroalstonine, occur in other genera of the family.
• Of particular interest is a group of about 20 bisindole alkaloids which contains those having
antineoplastic activity, including
– leurocristine (vincristine) and
– vincaleukoblastine (vinblastine).
– Vinblastine is produced by coupling of the indole alkaloids catharanthine and vindoline,
both of which occur free in the plant.
– Vincristine is structurally similar to vinblastine, but has a formyl group rather than a
methyl on the indole nitrogen in the vindoline-derived portion.
– vincristine is obtained in about 0.0002% yield from the crude drug
• In addition, there is a growing demand for vincristine rather than vinblastine, but the plant
produces a much higher proportion of vinblastine.
• Fortunately, it is now possible to convert vinblastine into vincristine either chemically, or via
a microbiological N-demethylation using Streptomyces albogriseolus.
38
Edited & Compiled by Dr M H Ghante

39. Alkaloids:Vinca
Uses.
Vinblastine is used mainly for the treatment of generalized
Hodgkin’s disease, and non-Hodgkin’s lymphomas.
• Vincristine is used principally in the treatment of acute lymphocytic
leukaemia in children.
• It has other applications for lymphomas, small-cell lung cancer,
cervical and breast cancers.
• The semi-synthetic vindesine is also used in the treatment of acute
lymphoid leukaemia in children.
• Vincristine has a superior antitumour activity compared to
vinblastine, but is more neurotoxic.
• Vinorelbine is a newer, orally active, semi-synthetic anhydro
derivative of 8′-norvinblastine with a broader anticancer activity
and lower neurotoxic side-effects than the other Catharanthus
alkaloids.
Uses.
Vinblastine is used mainly for the treatment of generalized
Hodgkin’s disease, and non-Hodgkin’s lymphomas.
• Vincristine is used principally in the treatment of acute lymphocytic
leukaemia in children.
• It has other applications for lymphomas, small-cell lung cancer,
cervical and breast cancers.
• The semi-synthetic vindesine is also used in the treatment of acute
lymphoid leukaemia in children.
• Vincristine has a superior antitumour activity compared to
vinblastine, but is more neurotoxic.
• Vinorelbine is a newer, orally active, semi-synthetic anhydro
derivative of 8′-norvinblastine with a broader anticancer activity
and lower neurotoxic side-effects than the other Catharanthus
alkaloids.
39
Edited & Compiled by Dr M H Ghante

40. Alkaloids:
Vinca, Rauwolfia, Belladonna, Opium,
Therapeutic uses
• As most alkaloids are extremely toxic, plants containing them do not
feature strongly in herbal medicine but they have always been important
in the allopathic system where dosage is strictly controlled and in
homoeopathy where the dose-rate is so low as to be harmless.
• These compounds are renowned for their potent pharmacological
activities.
• Whilst tiny amounts of some can immobilize an elephant or a rhinoceros,
others have important clinical use, such as
– analgesics, antimalarial, antispasmodics,
– for pupil dilation, treatment of hypertension,
– mental disorders and
– tumours.
Therapeutic uses
• As most alkaloids are extremely toxic, plants containing them do not
feature strongly in herbal medicine but they have always been important
in the allopathic system where dosage is strictly controlled and in
homoeopathy where the dose-rate is so low as to be harmless.
• These compounds are renowned for their potent pharmacological
activities.
• Whilst tiny amounts of some can immobilize an elephant or a rhinoceros,
others have important clinical use, such as
– analgesics, antimalarial, antispasmodics,
– for pupil dilation, treatment of hypertension,
– mental disorders and
– tumours.
40
Edited & Compiled by Dr M H Ghante

41. The major pharmaceuticals exported from India in the recent years are
1. Isabgol,
2. opium alkaloids,
3. Senna derivatives,
4. Vinca extract,
5. cinchona alkaloids,
6. ipecac root alkaloids,
7. solasodine,
8. Diosgenine/16DPA,
9. menthol, gudmar herb,
10. mehndi leaves,
11. papian,
12. rauwolfia,
13. guar gum,
14. Jasmine oil,
15. sandalwood oil, etc.
Alkaloids:
Vinca, Rauwolfia, Belladonna, Opium,
The major pharmaceuticals exported from India in the recent years are
1. Isabgol,
2. opium alkaloids,
3. Senna derivatives,
4. Vinca extract,
5. cinchona alkaloids,
6. ipecac root alkaloids,
7. solasodine,
8. Diosgenine/16DPA,
9. menthol, gudmar herb,
10. mehndi leaves,
11. papian,
12. rauwolfia,
13. guar gum,
14. Jasmine oil,
15. sandalwood oil, etc. 41
Edited & Compiled by Dr M H Ghante

42. References & Credits
• TEXTBOOK OF PHARMACOGNOSY AND
PHYTOCHEMISTRY- Biren N. Shah & A.K.
Seth, First Edition 2010, ISBN: 978-81-312-
2298-0
• TEXTBOOK OF PHARMACOGNOSY AND
PHYTOCHEMISTRY- Biren N. Shah & A.K.
Seth, First Edition 2010, ISBN: 978-81-312-
2298-0
42
Edited & Compiled by Dr M H Ghante